Hauling a flip over shack
I used to be able to put my power auger, a heater, one seat, and 3 five gallon pails in mine standing up and still get the cover it came with on. Now I have a carrier on my atv that the auger sits in so that freed up a ton of room in my shack. For me it works better to load all your gear up first and then put the seats in last on top upside down, they take up to much space in their sitting position.
If you don't want anything on the cover, get a second otter sled and pull it behind your flip over, but again, I wouldn't worry about some gear being on the cover.
I would rather a pail or my auger sit on the cover on the inside than have some of the cover be hanging outside and drag across the ice while transporting. That will wear a hole in it mighty quickly.